He knew how to argue. Then he learned how to listen.

During an internship at Manhattan Criminal Court, Long stood near the corridor leading to the Department of Corrections. The people he saw there did not fit the simple categories he had carried into the building. He left with a question that debate alone could not settle: what happens when someone leaves custody and tries to return to ordinary life?

Long was already good at gathering people around an idea. At Brooklyn Latin, he had founded a debate team. He had worked in local politics and youth advocacy, learning how to speak to institutions and organize other students. But he wanted that energy to reach someone beyond a hearing room or a tournament. Reentry gave the question a human shape, and friends gave him a team to act on it with.

Listen before building

The first answer would have been easy to invent. People leaving Rikers Island might need housing, mental health support, work, or a phone. Long and his friends instead tried to hear from people closer to the problem. Through nonprofits, they sent surveys into Rikers and waited for responses. Some came back almost empty. Others made one need impossible to ignore: contact with family and a way to navigate the first days after release.

What would it take to make the first call home possible?

That question narrowed SecondStart from a broad wish to improve reentry into something a student team could actually do. They raised money, arranged phones for people after release, sent resource texts, and donated books. Long had to find volunteers, work through partner access and legal constraints, and ask people in his network to back a cause they did not all understand at first. A mentor connected him with an experienced lawyer who helped the team navigate the work.

A project that taught its founder

The practical work was not glamorous. It meant organizing friends around follow-through, finding partners who could reach people the team could not, and learning that a small delivery only matters if it reaches the right person. The team also donated more than 75 books to Rikers. The stronger lesson was about sequence: listen, identify a workable need, bring people together, and then test whether the help lands.

Long wrote about the team's SecondStart work in his college application. In a Penn supplement, he connected what he learned to questions about policy visibility and said he hoped to work with Penn's Pardon Project. He also named Civic House's Community Engagement Program as a place to continue learning from Philadelphia organizers. Those were ambitions in his application, not claims that he joined either program.

Long later received a full scholarship to the University of Pennsylvania. SecondStart gave him a real account of what he noticed, built, learned, and wanted to do next.